Dilemma Podcast

Donald Trump is often mocked for his bluntness, but what if his “no more bullshit” approach is actually revealing something deeper—something that both leftists and Trumpers can recognize about the world order? In this video, I break down what Trump’s honesty really exposes, from his bizarre Greenland purchase idea to his “Gaza Riviera” plan, and how it all connects to the long-standing contradicti...

In this video, I sit down with journalist and whistleblower Jack Poulson to uncover the hidden world of surveillance, data brokers, and the quiet war on dissent. We explore how pro-Palestine protesters are being tracked, the real-time auctions selling your personal data, and the murky alliances between Big Tech, intelligence agencies, and the military. Jack breaks down the mechanics of AI-powered...

In this video, I sit down with journalist and author Anjan Sundaram to explore the crisis of journalism, the emotional strain of witnessing trauma, and the uneasy coexistence of catastrophe and daily life. We discuss how the news is shaped, the search for the “perfect victim,” and the geopolitical narratives that demand palatable symbols of justice. Anjan’s insights are paired with an essay on the...

In this video, I sit down with scholar and author A. Dirk Moses to unpack how the merging of the Holocaust’s specific history with the generic concept of genocide—and its elevation to the “crime of crimes”—has shaped our collective imagination in ways that blind us to potentially far worse horrors. Moses explains how the pursuit of permanent security by states and groups enacts devastating violenc...

In this interview with Stavit Sinai, we explore her journey from growing up in a Zionist environment to avoiding conscription in the IDF, and the challenges she faced, including accusations of antisemitism for her activism. I also provide an in-depth breakdown of the psychological phenomenon of cognitive dissonance and its relevance to these complex issues. 00:00 Introduction 04:19 Born to Holocau...

Vijay Prashad and I discuss the fierce defiance of the Global South, from the legacies of leaders like Kwame Nkrumah to the global conversation about neocolonialism. We dive into the new mood of the Global South after October 7th, the fight for dignity in places like the West Bank, and the global power dynamics that continue to shape these battles. whatjaythinks.com 00:00 Pop Quiz Introduction 03:...

A reflection on my first trip abroad, where I first learned the name Kwame Nkrumah and started wondering why things were the way they were. An effort to broaden the conversation from Palestine, exploring the tangled relationship between peace, justice, free will, the principle of Unjust Riches and the impact of the past year’s global events.

An examination of the intertwining of Zionist ideology and symbology in my upbringing in Judaism. What Kamala was talking about when she spoke to AIPAC. And who I am voting for in the US elections.

An essay which takes this question seriously. 00:00 Introduction 01:00 What does condemn mean? 02:46 Condemnation and victims statements 08:54 Two paths to being condemned 11:11 Do I condemn the condemned? 12:06 Children aren´t condemned 13:23 Nemr´s Pain 16:51 Doesn't delegitimize 19:05 Native American Analogy 21:00 Manifest Destiny 23:50 Would you argue against the Trail of Tears? 26:48 The...

Jay discusses Palestine with historian and author Ilan Pappe. Together they ponder if we are seeing the end of Zionism and what might that collapse might look like. Jay then reads an essay on the topic of forgiveness and redemption and how the psychology of cognitive dissonance prevents us from having evidence change our mind.

In the final part of this series, Jay dissects the definition of the words Zionism, Israel, and Judaism and delivers a Speech he wishes a future Prime Minister of Israel would give. The entire collection and all resources can be found here: whatjaythinks.com

A conversation with Miko Peled on his journey from unquestioned Zionism to becoming an active Palestinian Activist. In this episode we discuss: Jacob Israel de Haan Where are the Palestinian Nelson Mandelas? How Miko changed his mind When the only thing left is violence Why Zionism is flawed from the beginning What the future might hold for Israel Zionism vs Judaism and more...

A conversation with Richard English who dares ask the question "Does Terrorism Work?" In this episode we discuss: The IRA The Troubles Hamas Al Qaeda Jewish Terrorists Whether Israel is an example of successful Terrorism The motivations of terrorists How to evaluate the success of terrorists Deciphering the intent of terrorists How terrorist motivations change when they take power and mo...

A conversation with Haaretz journalist Gideon Levy where we take the pulse of Israel and discuss how he came to question the Zionist project and where we might go from here. In this episode he discusses: Two State Solutions What Israelis know How America ruined Israel Why journalists censor themselves The power of American Jews to change things If there is any hope Does Israel have a plan? More in...

Jay Shapiro breaks down arguments being presented by popular thinkers such as Sam Harris and from Zionists who defend Israel. He walks through the complications of deciphering the popularity of Islamism and Jihadism and Hamas and he outlines the mentality of "tribal essentialism".He teases a trilogy of upcoming episodes with Gideon Levy, Richard English, and Miko Peled. In this episode h...

David Livingstone Smith has been studying "dehumanization" for decades and has written three books on the subject. In this episode Jay and Smith apply his findings to the current conflict in Israel and broaden their scope to examine how a rising modern factor of "Distance" interplays with violence.

Jay Shapiro's personal essay and account of how the disfigurement of American Judaism has forged an existential crisis for something much bigger than survival of the state of Israel.

A nuanced look at the morality of intentions and self-deceptions in the Israel Palestinian conflict. A look at the moral distinction between collateral damage, intentional civilian targeting, and something much more common and psychologically complex which the Jewish experience makes Israel particularly suspectable to. Referenced in this episode: The Rest Is Politics - Husam Zomlot The Rest Is Pol...

Is there any hope for that strained or broken relationship that's become a causality of the political divide? Is common ground found best by going towards our superficial commonalities or in the direction of our deepest existential fears and hopes? Are the toxic business models of social media too much for us to overcome? Monica Guzman is the blue leaning daughter of two Trump voting Mexican immig...

What is it like to be a baseball bat? This episode is a dive into the philosophical approach known as Object Oriented Ontology (OOO) with the author and philosopher Ian Bogost. Ian Bogost is a video game designer, author, and philosopher known for his most recent book Play Anything , but this episode is all about his book Alien Phenomenology: or What is it Like to be a Thing?

How many countries are there? 197? 193? 180? It depends who you ask and who is counting. What constitutes a "state"? How does that differ from a "nation"? Why do certain claims of self determined statehood go unrecognized while others are accepted and others are disputed. How do we respond to Putin's actions in Ukraine? How does the diminished and tarnished role of US global leadership affect worl...

Does 2+2 really equal 4? What realm of truth am I in when I speak about my pain? What kind of truth claim is it to speak about the existence of "Poland"? How about the existence of ghosts and gods? Spencer Greenberg breaks down his taxonomy of truth claims to help us better understand what we and others might be saying when we declare something to be true. He also lays out his personal philosophy...

Is it possible that the default position of libertarianism which has so deeply influenced politics, economics, and philosophy since the enlightenment could produce an ecosystem which stalls our ability to handle the existentially daunting task of freedom? Does the political structure of libertarianism dissolve into a fantasy the moment it encounters a problem of the commons like COVID or climate c...

What if much of what we do to our children works directly against what we profess we ultimately want for them? Alfie Kohn argues that things like homework, grades, systems of praise and punishment, reward and sanction, and generally the enforcement of an atmosphere of fierce competition in education all undermine our stated goals. So are the goals wrong? Are the goals false? Or is something much m...

Is abortion ever morally permissible? Is it always wrong? Are there any morally valid exceptions? Do any if the answers to these questions demand a certain kind of legal limitation? Where and how do we ground any of these contemplations? In this philosophical dive into the fraught issue of abortion, Jay tangles with Bethel McGrew (Esther O'Reilly) who brings her deeply Christian perspective to the...